Richie's Mom
Copyright© 2026 by cv andrews
Chapter 5
Erotica Sex Story: Chapter 5 - "My mom's got a crush on you." That's what my best friend Richie said one night when we were just hanging out in my back yard. "Davey, my mother's got a serious crush on you” Of course I was sure he was just clowning around, fucking with me just for the heck of it. I mean, sure, I'd known Richie's mom for ages, since we were seven and in the second grade, and yeah, she's real cute and I've seen her in a bikini and she's got a great body and stuff. But, c'mon – Richie's mom...?
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa mt/ft Ma/ft mt/Fa Fa/Fa Fa/ft Consensual Lesbian Heterosexual Fiction Sharing Incest Mother Son Sister Father Daughter Gang Bang Group Sex Swinging Anal Sex Analingus Double Penetration Fisting Oral Sex Squirting Teacher/Student
“Is Richie...?” There wasn’t any need for me to finish the question.
“Yes,
“He is – he does.”
“Do you want to continue watching, David?”
Yes.
I want to keep watching.
The scene changed – it looks like it might even be a different... occasion? And the first thing I see is my mom, and she’s lying on her back on a big cushion and she’s fucking some guy, and it doesn’t look like Ed Conner, and I know by now that it’s not my dad. This guy looks younger, maybe my and Richie’s age, or may a few years older, and my mom has her legs around him, and it looks like they’re enjoying each other – a lot. But like I said, he wasn’t in the other video scenes.
“Who’s the guy that’s...,” I never thought I’d be asking this question, “Who’s the guy my mom is fucking.”
She hesitated for a second, but then said, “That’s Van’s brother, Ted.”
So both Van and her brother are also part of this... sex group ... with my Dad and Mom and Ed and Val ... and Carole?
So I watched, watched Ted Conner, Richie’s girlfriend’s brother. Only now he and Mom aren’t fucking anymore. Now he’s straddling her and he’s fucking Mom’s mouth. (Holy shit! – I can’t believe I just said that some guy is fucking my mom’s mouth!!) And he makes one last lunge into her mouth, and he must be in her throat by now and her fingernails are digging into his butt and he keeps thrusting into her mouth. And I can actually see her throat gulping and it’s obvious that she’s struggling to swallow the load of cum that he’s emptying into her throat.
And she’s not trying to get away! She’s trying to swallow his huge load – and she’s loving it!
I jerked my head away from the TV and looked at Carole. She stopped the video and turned to me...
And she kissed me, a gentle, reassuring kiss.
Because she knew that that’s what I needed – reassurance.
“David, how are you feeling – about what you just saw?”
How do I feel?
I couldn’t seem to find the words to describe my feelings. Because my feelings were... ambivalent.
Somehow, Carole seemed to know.
“You never saw – never thought of your mother... ‘that way,’ did you, David? Never thought of your mother as ... as a woman. She was always a ‘mom,’ right? And moms don’t do things like ... that.
“But you’re excited as hell, aren’t you?
“I mean, watching a hot woman getting fucked by a good-looking young stud? Don’t try to deny it, David. I was watching your face while your mother was getting fucked, ... and watching your cock, too. You were getting turned-on.”
I opened my mouth to protest ... but then realized – that would be pointless under the circumstances.
“No, don’t try to deny it, David – seeing your mom loving getting fucked by Ted Conner was turning you on, wasn’t it?”
And I remembered – that’s exactly what I saw when I watched the video – that my mom was loving it – loving what that stud was doing to her, or made her do. And I didn’t have to say it. Carole already knew.
But she wasn’t going to rub it in. She kissed me again, this time playfully.
“Besides, David – by now you should know – moms do do things like that, because if they didn’t, then you and I wouldn’t be here, would we?”
Oh, yeah. I kind of forgot.
Then Carole added, “Besides, it was pretty hot, your mom and Ted, wasn’t it,” and clicked the video back on.
There’d been a break in the action and now the camera was focused on a threesome of Carole, on her back and Dad’s fucking her while she’s eating Mom’s pussy, and I could hear my dad saying, ’”Take it, bitch – take my big dick,” and my mom’s voice telling her how good she was eating her and how Mom was “gonna squirt my cum in your fucking mouth, you little slut!”
The camera stayed on them long enough for Dad to cum in her and I guess for Mom to squirt her cum into Carole’s fucking mouth. Then it swung slowly to two couples that were on a bunch of cushions spread out on the floor. Both of the guys were lying on their backs and the women were riding on top of them.
And “riding” is definitely the word. Moving up and down, tossing their heads, working their hips around and back and forth. Even in the dim lighting I could see that one of the women had a blond ponytail.
Then the video moved to where you could see their faces...
... and I immediately recognized Van, Richie’s girlfriend. And the guy she was on top of was the same young guy that I watched fucking my mother earlier in the video. (Or maybe I should just accept the fact that Mom was fucking him every bit as much as he was fucking her.) Yeah, the guy Van was riding was Ted, her brother.
Then the camera turned to the other two people, and by now I’m able to recognize Mrs. Conner – Val, Van’s mother. And the guy she’s riding on is Richie.
Yeah, Richie – my best friend for 12 years – her daughter’s boyfriend.
And that’s when it finally got through to me: That for these people, when they are together like they are in these videos, that anyone can fuck – or anything – with anyone – and did.
And that includes, I guess, Carole.
My Carole.
My Carole?
She started the video again. It must have been a little later, and now I recognized Mrs. Conner. She was on her knees and getting it from behind from some guy, and again the guy looked like Ted Conner. Is that what I was watching – hot Mrs. Conner, getting fucked by her own son?
And all of a sudden I wondered, what did that mean for me? Does that mean that it’d be okay for me to fuck Mom? Or that maybe I’d even be expected to?
And I remembered how hot Mom looked in that first video, when she first took off her robe and turned around, and how hot she looked when Van’s brother Ted was straddling her with his cock down her throat...
... and the recording went black at that point, and Carole pressed the Stop button on the remote and turned off the TV.
And we just sat there like that, until Carole said, “Is there anything you want to talk about?”
Was there? Is there?
“Is there something you want to ask me, David?”
I guess the very first thing was, “Why did you want me to see these ... videos?”
She took a deep breath, then waited, like she was collecting her thoughts or trying to decide what to say, or maybe she knew what she needed to say but not how to say it. I guess she finally got her words together.
“David, you needed to know this, about me. And not just that I did these things, but that I needed to do them. I needed the sex ... but I needed the human contact just as much.
““Even before he died, life with Richard’s father was – unusual. We were almost completely estranged from each other. There wasn’t any hostility between us, mainly because he wasn’t really ‘there” enough for there to be anything to be hostile about. And then when he died – and the way that he died – it left me completely empty. Richard was a godsend, and he was wonderful, but I still felt completely... hollow.
“And I went like that for more than a year after he died, and that plus the years before ... And I guess it took another woman to see, because that’s when your mother had that conversation with me and suggested that she understood what I needed, and that she had an idea that might help.
“You already know most of that. But what you asked was why I wanted you to see these. And the answer, I guess, is simple – you had to know. If we’re to be together at all then you have to know – that I’ve done these things, and why?
“So now I have to ask ... David? Can you still love me? Can you still be together with me?”
And she waited for me to answer. And I could see it, in her face and in her body – the anxiety – the fear.
I think she was 51 percent sure that my answer would be yes – yes, I can still love her, yes, I can still be with her...
... but also 49 percent afraid – afraid that I’d say no, “No, I can’t be with you...”
So ... how do I feel?
It wasn’t that difficult. Not difficult, because I’ve been grappling with that question since that first moment I witnessed her in that first video.
And the answer is “Yes.”
Yes, because videos or not, Carole Wilson is the woman who loves me, and still the same woman who played such an important role in my life all the years that I was growing up – or trying to grow up – and who helped make me the person that I am. And who over all those years became my idea of how a girl, and later, a woman, should be.
But how about the sex?
So, what about the sex? I was never hung up on the idea that I should find someone who’s a virgin. And, I mean, Carole was married and has a child, so I was pretty sure from the start that she wasn’t a virgin.
Okay, then what about the videos, of the group sex? Certainly that should be a deal-breaker, right?
So what if after Richie’s dad died, that instead she’d “dated” a bunch of guys – maybe dozens, maybe even more. And maybe some of them might not have been so “admirable,” maybe even getting her into risky stuff, or maybe some really sick shit? Somehow that would have been better – more “acceptable” – than her getting together with a group of solid, sober, responsible people like my parents, and even the Conners, who knew what she’d been through and cared for her and would look out for her?
No, what’s past is past.
But, ... where do things go from here?
“Carole, do you...,” and I couldn’t make the rest of the words come out.
She put her hand on mine.
“You want to know ... want to know if I want to keep going ... to ... those... evenings – is that right, David, you want to know that?
Yes, I did want to know that. Had to know ... did she still want to...?
“You should know – I haven’t done ... anything ... gotten together ... since that very first night you and I kissed ... And you know I haven’t had time for anyone – or anything – else since we’ve been together...” She laughed and playfully punched me.
And at that moment I loved her so much.
But the other part – does she still...?
“But you want to know the other part, don’t you? Well, I won’t lie. Yes. Yes, I still want to ... want to.
“I’ve tried to find words to explain why. First, don’t ever think that there’s some way that you’re not ‘good enough.’ You’re perfect, David, and I love how you love me and how you fuck me and how we make love. You are perfect to me – there is not a single thing that’s... missing with you. To me, David, you are perfect.
“But with ... the others, with them, when we’re all together like that, like you saw in those videos, it’s exciting. I thought I’d try to explain it to you. But in fact, I don’t have to, do I, David? I don’t have to explain it to you ... because you’ve felt it. You felt it yourself. And I know, and I know that you know, because I’ve watched you. And I’ve seen you. I even saw you getting hard when you were watching Ginni – your mom – fucking Ed and Ted Conner..., and even your dad.”
She reached over and grabbed my cock, which had gotten hard just while she’d been talking.
“Admit it, David,” she leaned over and breathed into my ear and gave it a warm, wet little lick with her tongue, “Admit it – seeing it gets you hard, doesn’t it. Even watching me turned you on, didn’t it? And you’re already wondering, wondering what it’s like, how it would feel...”
And like almost everything else, she was right about this.
She was right – that I sensed and understood the excitement of the whole thing. And she was right – that even just watching the dimly-lit videos got me turned on, and even seeing Carole, and how sexual she is, and how the others desired her, and even my mom and Van...
And seeing how sexual my mom was – is,,,
And how just sitting here talking about it gets me hard...
So, yeah, I understand...
So, ... what now...?
“David?”
“Yeah?”
“David, so you want to fuck...?”
~ ~ ~
So now I have to decide.
Carole said that now that she and I are together, that she didn’t need ... the “time” with my mom and dad and the Conners.
But the way she said it, she emphasized the word “need” – that she didn’t need to... “get together” with mom and dad and the others.
But the way she said it, it was obvious – she wanted to.
Yeah, Carole – my Carole – wants to continue, to keep having group sex with my parents and the Conners – and maybe other people?
Also, with the implication that she wouldn’t be doing it alone. Implicit in her words, or maybe not so much in her words as the way that she said them, that I would be a part of it with her.
And I didn’t think there’d be any way that I’d just be standing around, jerking off or something while all kinds of sex was going on around me. I think Carole clearly thought that I would participate – that while Carole was sucking Mr. Conner and getting fucked by my dad, that maybe – probably – I would be doing stuff with sexy Mrs. Conner...
... or Van,
... or my mom...
... or maybe both!
Were they – was Carole – really suggesting – inviting – me into a situation where I would be fucking my own mom?
That would be... gross – gross times ten!
And then I thought about how she looked when she took off her robe and I didn’t know it was her, and then she turned around. And then in that later video, and how hot she looked when Ted Conner was straddling her and she had her mouth around his cock...
And how hot she looked when Carole was eating her pussy...
And then I remembered that later video, and how Ted had his mom on her knees and was giving it to her from behind. Yeah, I was watching my hot second-grade teacher getting fucked in the ass by her son.
And did that mean that it’d be okay for me to fuck Mom? Maybe even be expected to??
It was three, almost four weeks later, when it finally happened.
“David?”
“Yes?”
“Your mother called. She was asking ... she said...
“Well, what she said was, they and the Conners would be... getting together ... this weekend. And she asked ... she asked if we ... if you and I ... would like to join them...”
So, this was it. Put-up-or-shut-up time. Despite my various rationales for doing one thing ... or the other, still, now was the time to actually do ... one thing or the other?
I had been both thinking about this time and dreading this time since shortly after Carole and I had “the talk” after watching that last video.
But I had already decided.
“Yes. Tell Mom...,” yes, Mom, “we’d like to come.”
And then, out of nowhere, I got this weird idea.
“Ask her what we should wear...”
~ ~ ~
Yeah, I had made up my mind shortly after that conversation.
First, most important, I was not going to do anything to make Carole feel that I rejected, or even disapproved, of the life that she lived after Richie’s dad died. We’d made commitments – I had made a commitment – that went a lot deeper than just who we fucked. I had committed myself to her – to Carole Wilson – just as she was – is.
The second consideration – and it was the secondary consideration – was, and this sounds really shabby, because it was exciting. It was exciting as hell. Yeah, I admit it. Even watching Carole getting fucked by other guys or my mom sucking a young stud’s dick – it was all exciting. And I could tell myself all the rationalizations I wanted – watching it still got me hard.
I won’t go into some elaborate build-up. We talked, and Carole told me what to expect, and how I felt about certain things, like my parents being there, and being around other guys who’re naked, and about seeing my mom – and seeing Carole.
And also, what we should wear. (Turns out, comfortable clothes, like you’d wear when you go over to friends’ house to visit, but also easy to get out of. And an appropriate cover-up. For easing into... things. And also, and I hadn’t even thought of this, if I get cold.)
And just before we were supposed to go over (to the Conners’ house this time – it was Mom who figured that doing my first time in my own basement rec room would feel weird to me) I was jittery as hell, like you would imagine. And then Carole said, “David, I got this for you,” and then she added, “ ... in case you get cold.”
She handed me a soft, kinda floppy package wrapped in blue tissue paper.
“Well – open it!”
The tissue came off easily, and in it was a really nice ... robe, I guess you’d call it, a real pretty turquoise blue.
“Try is on.”
I unfolded it and slipped it on over my shirt and slacks. It seemed like some kind of soft modern “miracle fiber” that was light but still warm and it fit fine. It wasn’t long enough to be a traditional bathrobe but wasn’t short enough to be called a “shorty” – it came to just about mid-thigh, and I thought that that was just perfect.
She stepped up and kissed me. “I thought the color would match your eyes.”
And at that moment I got one of those feelings – that I love this woman so much...
And that no matter what happens this evening, it’ll all work out right.
Of course I was nervous!
Carole drove us over, one, because she knew I was nervous, and two, because I’d never been to the Conner’s house and she knew the way.
When we arrived, Mr. and Mrs. Conner – Ed and Val – greeted us and welcomed us just like you would any friends. And they were still dressed, pretty much the way Carole and I were. They offered us drinks and we said yes – “but not too strong,” and Mr. Conner – Ed – said “Of course.”
“David, your mom and dad are already downstairs. Maybe you’d like to go change into something more comfortable? Carole, you know where the guest bedroom is...”
Just as I was turning to follow Carole, Ed Conner put an arm around my shoulder and held out his other hand. In his fingers was a little blue pill, one I’ve never seen but definitely knew “by reputation” (I’d never needed anything like that with Carole).
“I have a friend who’s a pharmacist. If you take this I think it’ll help you enjoy the evening ... even more.”
I never in my life ever thought about taking an ED pill (like I said, never necessary with Carole!). But since I was a “rookie” I thought I should take a tip from someone who’s experienced in this ... kind of thing. Also, it was really nice of him to think of me, and what it’d be like for me – and for doing it so nicely. And I had this thought – I like this guy.
So I went into the room where Carole went. She had already changed into a lovely satiny wrap in a kind of red color she once told me was called fuchsia. And she looked radiant, and beautiful, and I loved her so much, and at that moment I was wondering why I would ever be willing to share her with ... share her with... anyone.